


Imagine You Introducing Dean to Pegging

by CrowleysBabe



Category: Supernatural
Genre: Anal Fingering, F/M, First Time, I tried do some kind of romance, Pegging, Porn Without Plot, Post-Coital Cuddling, Top!Reader, bottom!Dean, but I not good at this, butt plug
Language: English
Status: Completed
Published: 2015-04-04
Updated: 2015-04-04
Packaged: 2018-03-21 07:10:10
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,412
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3682764
Author URL: https://archiveofourown.org/users/CrowleysBabe/pseuds/CrowleysBabe
Summary: <blockquote class="userstuff">
              <p>Y/N and Dean had been togheter for a while and she wants to try something new</p>
            </blockquote>





	Imagine You Introducing Dean to Pegging

**Author's Note:**

> This one goes to one of my best friends. We were talking about pegging and she said:  
> "Hey, imagine you introducing Dean to pegging"  
> I did. So I wrote this in my first language and showed her. And now I'm gonna show you!  
> Hope you enjoy!!

Y/N is in the motel. Sam in the other room and Dean's taking a shower.  
That's everything she needs. Being alone to think.  
Y/N and Dean had been doing their kinks for a while.  
Dom/Sub, Pet/Owner, Daddy-Mommy/Little girl-boy, Slave/Master-Mistress, Teacher/Studdent, etc. etc.  
All new things.  
Y/N had been a naughty little girl who needed a spank.  
Dean had been a very bad pet, who Y/N needed discipline.  
Once, Dean locked Y/N up in a dungeon, called her 'slave' and fucked her in so many diferent ways.  
After that, Y/N was a very strict teacher who gave to her brat student a harsh canning.  
And a lot of other things that they wanted to try. But there's one thing that Y/N wants to do with Dean.  
It's not something new. It's very old to her. Some kind of fetish of hers. She has a lot of practice. But Dean never had done that. And Y/N is afraid of scary him. 'Cause it might look... well, not so good as it is.  
Why would he say? Y/N bites her lower lip and try think.  
But it's too late. Dean came out of the bathroom.

"Dean, can we talk?", she asks. Before she could give up

"Sure, sweetheart", Dean answer, drying himself in the towel. "Let me dress up first and we'll talk"

"Okay", she answer and try control the butterflies in her stomach.  
Y/N watches Dean's naked and wet body get dry and dressed. She loves watch him. He's tall and handsome as hell.  
His body is like a soldier's body. He got those muscles fitghing, running and digging craves. He is a soldier who always had been in war.  
Dean sits down next to her. His hair still a sexy wet mess.

"We can talk now, sweetheart", he says, putting her hair behind her ear

"Have you ever heard about pegging?", Y/N asks, bitting her lower lip. It's better this way. Go straight to the 'thing' while she's still brave enough to ask.

"Yeah! Why? Are you into it?", he ask. Dean seems really okay about it.  
It's not so bad, Y/Y thinks.

"Yeah. I do", she answer, blushing a little bit. "And I want to do with you", Dean had his atention on her. Listening, trying understand. "If you don't want, it's okay. If you want, I promise that I'll go slow and calm with you. And, of course, we'll use the safeword"

He looks down, thinking. Y/N feels her heart beating really fast and bite her lip so hard that soon enough it'll bleed.

"Okay. I'll do it", he says, looking up to her. "I'll do it. If I don't like, we'll stop, right?", Y/N nods. "So, why shouldn't we not to try?"

She gives him a small smile. And hold his hand, interlacing her fingers on his.

"You might be a little bit sore tomorrow", she says. He need to know. And she won't lie to him. This works based on mutual trust and respect. Lies would screw this up. Would have broken the trust, respect, love and everything else that keep it up. Dean trusts her - so, Y/N would never lie to him - and she trusts him, that's all what matter to them.

"Okay", Dean answer.

******

After a few minutes, Y/N got the smallest butt plug that she has and lube. Dean is sitting down in the edge of the bed, naked and waiting for her firsts orders.  
'Cause today, she's in the charge.

"I'm not gonna tie you up today", she says, sitting down next to Dean. "But you're going to be blindfolded. But no gags, neither handcuffs. Okay?"

"Yeah. Okay", he answers. He's tensed and nervours. She knows how Dean is with new things - he's very scared at first and then relax - and she wants to make him feel safe.

"Ready?", she asks and put a blindfold covering his adorable green eyes

"Bend over the bed", Y/N orders, softly to make sure that she won't be harsh.  
He obeys and waits.  
And then, Y/N pass a lot of lube on her fingers and in Dean's anus too. And slides one finger inside.  
He gasps and goes tensed all over. And pushes his hips back. It hurts a little, but he can't lie to himself and say that's not good.

"You okay?", she asks, biting her bottom lip

"I'm fine", he answer, trying relax and breathe.

She moves her finger in small circles and wait for him to adjust. When he's comfortable, Y/N slowly adds a second finger. Always calm and taking easy.  
She's always rough, but not today. Today she's gentle and kind. And Dean appreciates that a lot.  
After a few minutes in this rate, Y/N alredy has four fingers inside him.  
Dean can't say that's bad. It hurts a little in the beginning but when he adjust to ther thrusts and the feelling of being full, it feels awsome.  
Y/N is always asking him how he feels or if it hurts too much.  
He's honest to her. They're honest to each other. And it's working.

"I'm gonna remove my fingers, alright?"

"Yes, Ma'am", he answer. Relaxing and trying open himself to her.

And, slowly, Y/N removes finger by finger. She doesn't try do it quick. She does it with patience to not hurt Dean's virgin and tight hole.  
When all her fingers are out, Y/N pass more lube in his entrace and in the plug.

"I'm gonna penetrat you using a butt plug", she says. He hold his breathe and she knows he's scared. "It's very small. Don't worry. But if you don't like it I'll stop"

"Y-yes Ma'am", Dean answer and swallow dryly.

Y/N put two fingers in his entrace and soon he's open to receive the plug.  
She pushes it inside him slowly and stopping to him adjust. He's doing just fine. And she keep going.  
But when the plug is all inside him, it hurts. Dean feels like he's gonna split him in the half.  
She's does it slowly, but still hurts.

"IMPALA! IMPALA!", Dean yells out. His safeword makes Y/N stop what she's doing and slowly remove the butt plug.

Y/N removes the blindfod and caresses Dean's back.

"It's okay, sweetie. It's fine", she leans in and kiss his shoulders blade. "You were doing okay. What happened? Did I hurt you?"

"Yes-No! No. It's just... I-I"

"Don't worry. It's fine. Do you want stop for the night?"

"...no. I... Talk to me, Y/N!", Dean asks. He's a little bit sore now and needs her.

"Of course, sweetie. Whatever you want", she answers. He has to feel safe and protected. 

"I want keep going... But... it's too big", Dean says, gasping. She keeps caressing his hair and face. He loves her gentle touch and closes his eyes.

"I'll see if I have something smaller", Y/N kiss him in the forehead and his eyes, pretty green eyes, fly open. "Are sure you want keep going?"

"...yes. But... keep this one, please"

"Dean..."

"I can do it, Y/N", Dean says, he wants to try.

"Are you sure?"

"Yes. If I want to stop I'll let you know"

"As you wish"

So, Y/N pass more lube in his entrance and in the plug and pushes it slowly inside Dean.  
She's going gently moving it when the plug is all in Dean's anus and put her other hand between his legs, fondling him. He's alredy hard when she rolls his balls and stroke his cock.  
She's getting wet while Dean is almost leaking. 

"Ma'am, may I cum?", he asks. His cock getting pink and harder.

"Of course", Y/N answer. "You're a good boy"

And them both cum with all their strengh.  
After a few seconds, Y/N removes the plug and clean Dean up. Being gentle and kind. He's sore and will be by tomorrow, so she has to take care of her boy.

"How are you?", Y/N asks, while her and Dean are cuddling in the bed and she caress his arm.

"I'm good, sweetheart", he answer, kissing her lips. "It hurts, but it was good"

"Will you want to do it again?"

"Maybe", he answer and laugh

It ain't something that he would ever say that he likes. But now Dean has to admit: Pegging is awsome.

**Author's Note:**

> I tried write some sort of romance in the end, but I'm not so good at this  
> sorry


End file.
